Isolation of tocopherol and sterol concentrate from sunflower oil deodorizer distillate
01 Oct 1996-Journal of the American Oil Chemists' Society (Springer-Verlag)-Vol. 73, Iss: 10, pp 1271-1274
TL;DR: In this paper, the isolation of tocopherols and sterols together as a concentrate from sunflower oil deodorizer distillate was investigated, which included process steps such as biohydrolysis, bioesterification and fractional distillation.
Abstract: The isolation of tocopherols and sterols together as a concentrate from sunflower oil deodorizer distillate was investigated. The sunflower oil deodorizer distillate was composed of 24.9% unsaponifiable matter with 4.8% tocopherols and 9.7% sterols, 28.8% free fatty acid (FFA) and 46.3% neutral glycerides. The isolation technology included process steps such as biohydrolysis, bioesterification and fractional distillation. The neutral glycerides of the deodorizer distillates were hydrolyzed byCandida cylindracea lipase. The total fatty acids (initial FFA plus FFA from neutral glycerides) were converted into butyl esters withMucor miehei lipase. The esterified product was then fractionally distilled in a Claisen-vigreux flask. The first fraction, which was collected at 180–230°C at 1.00 mm of Hg for 45 min, contained mainly butyl esters, hydrocarbons, oxidized products and some amount of free fatty acids. The fraction collected at 230–260°C at 1.00 mm Hg for 15 min was rich in tocopherols (about 30%) and sterols (about 36%). The overall recovery of tocopherols and sterols after hydrolysis, esterification and distillation were around 70% and 42%, respectively, of the original content in sunflower oil deodorizer distillate.
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04 Jun 2013
34 citations
TL;DR: In this article, a 1:1 (w/v) ratio of PFAD and water mixture achieved its equilibrium after 5 h of reaction at 65±1 °C.
33 citations
TL;DR: In this paper, a new method for isolating sterols from sunflower oil deodorizer distillate (DOD) was developed, which is unlike most alternatives, it requires no distillation, and uses methanol in the presence of p-toluenesulphonic acid as catalyst to convert free fatty acids and acyl glycerides in DOD into fatty acid methyl esters (FAMEs).
32 citations
TL;DR: In this paper, the enzymatic esterification of free fatty acids from soybean oil deodoriser distillate with ethanol, catalysed by immobilised fungal lipase, was studied.
Abstract: The enzymatic esterification of free fatty acids from soybean oil deodoriser distillate with ethanol, catalysed by immobilised fungal lipase, was studied. The extent of conversion of free fatty acids to ethyl esters was optimised using a response surface methodology obtained through a second-order factorial experimental design. The variables studied were reaction temperature (30-70°C), enzyme concentration (7-23%) and ethanol/free fatty acid molar ratio (0.3-3.7:1). The optimal reaction conditions achieved were temperature from 46.4 to 53.6°C, enzyme concentration from 13.6 to 16.5% and ethanol/free fatty acid molar ratio from 1.7 to 2.3:1, with conversions above 88%. No significant tocopherol losses were observed during the process. In conclusion, enzymatic fatty acid esterification was shown to be a technically viable process. Le distillat de desodorisation d'huile de soja est un sous-produit valorisable: C'est un melange complexe d'acides gras libres, de sterols et de leurs esters, de tocopherols, de glycerides et d'autres composes. Il est ainsi la matiere premiere principale pour la production de vitamine E. Pour concentrer les tocopherols et le sterol, le procede enzymatique, par une lipase, d'esterification des acides gras presents est plus interessant que le procede chimique. Dans cette etude, les conditions du procede d'esterification enzymatique sont optimisees pour la production d'esters ethyliques par la methode des surfaces de reponses. Les resultats montrent que l'esterification enzymatique des acides gras est un procede techniquement viable.
32 citations
Patent•
29 Aug 2002
TL;DR: In this paper, a method for recovering fatty acids, tocopherols, and sterols from a distillate obtained from the deodorizing of various oils is described.
Abstract: This invention relates to methods for treating distillates obtained during the process of deodorizing various oils. More particularly, this invention relates to methods for recovering fatty acids, tocopherols, and sterols from a distillate obtained from the deodorizing of various oils.
32 citations
References
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Book•
01 Jan 1990
5,013 citations
TL;DR: In this article, a model mixture of pure oleic acid and dl-α-tocopherol was used to study any potential side reactions that may lower the tocopherol content during the esterification reaction.
Abstract: Separation of sterols and tocopherols from fatty acids in deodorizer distillate was facilitated through lipase-catalyzed modification of fatty acids in canola, mixed and soya deodorizer distillates. The fatty acid esterification with methanol catalyzed by SP-382 (an immobilized nonspecific lipase) proceeded rapidly, with conversion of fatty acid to methyl ester in 5 h being 96.5, 83.5 and 89.4%, respectively. A model mixture of pure oleic acid and dl-α-tocopherol was used to study any potential side reactions that may lower the tocopherol content during the esterification reaction. Under the conditions employed, the loss of tocopherol was less than 5%. Simple vacuum distillation (1–2 mm Hg) was employed to remove the volatile fraction (methyl esters of fatty acids, some fatty acids and other volatiles) of the esterified deodorizer distillate, leaving behind sterols, sterol esters and tocopherols. Sterols and tocopherols were almost completely retained in the residue fraction with recoveries in the range of 95%. Overall recoveries of sterols and tocopherols after esterification and distillation were over 90% for all the deodorizer distillate samples.
81 citations
"Isolation of tocopherol and sterol ..." refers background or methods in this paper
...This type of oxidation loss during esterification and distillation was reported by Ramamurthi and McCurdy ( 5 )....
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...Ramamurthi and McCurdy ( 5 ) esterifled the deodorizer distillate with methanol with a nonspecific SP 382 lipase, and about 4-10% fatty acids were retained in the reaction mixture....
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...Recently, Ramamurthi and Mc-Curdy ( 5 ) have tried to concentrate sterols and tocopherols from canola deodorizer distillate (which contained initially 1.00% w/w tocopherols and 1.58% w/w sterols) and soybean deodorizer distillate (initially containing tocopherols at 12.74% w/w and sterols at 11.39% w/w) by an enzymatic process....
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TL;DR: In this paper, the feasibility and technical merits of supercritical fluid extraction (SFE) as a potential alternative to molecular distillation for enriching tocopherols effectively from soybean sludge were examined.
Abstract: Supercritical fluid extraction (SFE) has been widely applied as a promising alternative to current extraction processes used in the food and pharmaceutical industries. SFE has some advantages over conventional separation processes such as liquid-liquid extraction, distillation, and adsorption. The most important advantage of utilizing SFE is the easy separation of the solvent from the extracted material without solvent residue. Further, supercritical fluids provide lower mass transfer resistance than those in conventional separation processes. A number of references dealing with the basic principles and applications of SFE are now available [1-3]. The objective of this study is therefore to examine the feasibility and technical merits of SFE as a potential alternative to molecular distillation for enriching tocopherols effectively from soybean sludge. In this regard, the solubilities of both sterol-removed soybean sludge and esterified soybean sludge in SC-CO2 were determined by a flow-through SFE system at temperature and pressure ranges f 35–70∘C and 200–400 bar, respectively. The tocopherol content in the extracts collected continously at equilibrium conditions up to the approximate 70 wt% extraction rate of the feed was checked by HPLC at each interval. The results of these initial feasibility experiments could provide fundamental information for the suitable application of a continous-type SFE for concentrating tocopherols.
70 citations
TL;DR: In this article, polyphenols were extracted from the rape of Israeli olive oil using hexane, acetone and ethanol in a simple sequential procedure yielding three fractions (A,B,C).
Abstract: Polyphenols were extracted from the rape of Israeli olive oil using hexane, acetone and ethanol in a simple sequential procedure yielding three fractions (A,B,C). Fraction A (extracted with hexane) contained few polyphenols (0.05%), while Fraction B (extracted with acetone) and Fraction C (extracted with ethanol) contained about 5% polyphenols each. Fractions B and C were also found to contain the highest ortho-di-phenol concentration (about 3%). The addition of purified Fraction B at a level of 100 ppm to refined olive or soybean oils partially inhibited the oxidative deterioration when the oils were stored in the dark at 100 C.
58 citations
"Isolation of tocopherol and sterol ..." refers methods in this paper
...Separation of sterols and tocopherols has also been tried by Sheabar and Neeman ( 3 ) with a combination of solvent extraction and chemical treatment....
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01 Apr 1992
55 citations
"Isolation of tocopherol and sterol ..." refers background in this paper
...Supercritical fluid extraction technology is promising, and attempts have been made to isolate tocopherols from soya sludge ( 4 ) by this process....
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